


Three Hundred Bucks

by Syracard



Category: Supernatural
Genre: Absent John Winchester, Acts of Kindness, Bad Parent John Winchester, Bisexual Dean Winchester, Dean Winchester Has Self-Worth Issues, Dean Winchester Takes Care of Sam Winchester, Dean Winchester is Sam Winchester's Parent, Dean doesn’t care about himself, Dean will do anything for Sammy, Episode: s04e01 Lazarus Rising, Gambling, Jimmy Novak is a sweetie, John Winchester's A+ Parenting, Kindness, Loss of money, Sammy comes first, Teen Dean Winchester, Teen Sam Winchester, attempted prostitution, eleven years later
Language: English
Status: Completed
Published: 2019-01-27
Updated: 2019-01-27
Packaged: 2019-10-17 12:45:33
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,662
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17560643
Author URL: https://archiveofourown.org/users/Syracard/pseuds/Syracard
Summary: After losing the rest of their money, eighteen-year-old Dean Winchester decides to sell himself and meets a man named Jimmy at a gas station.





	Three Hundred Bucks

_**1997** _

 

Dean should have never left the room. If he stayed in the room with Sam, then he wouldn’t have gambled away the rest of the money their dad gave him. He had two hundred bucks left, and he thought he could win more and buy him and Sammy something nice without dad knowing. And in the blink of an eye, he lost it all.

Dad’s gonna kill him when he gets back.

 

\\\\\\\\\\\\\\\\\\\•//////////

 

“What’s wrong?” Sam asked as he studied his older brother. They had been watching some scary movie on TV, and it was clear that something was bothering Dean.

Dean looked over at him and asked “Hmm? Oh, nothin’. Don’t worry about it.”

He turned his attention back to the TV and after a moment of silence, Sam said “I know you’re lying.”

The older brother looked back over at San and smiled. “Alright, you got me...I’m just worried about dad, is all...”

“Me too. Did he call you?”

“Nope. But he’ll be fine...Hey, I’m gonna walk down to that gas station and pick up some snacks. Want anything?”

The younger brother shrugged and said “Surprise me.”

Dean got up and grabbed his jacket, turning to Sam while he put it on. Then he came over and said “Now remember. Anything comes in here that isn’t me or dad—”

“Shoot first, ask questions later, I know.”

He smiled at his little brother and ruffled his hair. “Good boy. I’ll be back soon, I promise.”

  
\\\\\\\\\\\\\\\\\\\•////////// 

 

The gas station was a ten-minute walk from the motel. Their dad had stopped there for gas before they found the motel, so he figured it was his best bet. _It’s no big deal_ , he told himself. _Tons of hookers do it every day, so can you. Just pretend they’re a pretty girl at school or something._ When he saw the gas station up ahead it was deserted except for a couple of cars.

One of the cars was parked at one of the pumps and he watched as a man came out of the station and walked up to it. From what Dean could see, he’s pretty cute, even though he was clearly a few years older. Dean is pretty into girls, but lately he’s been feeling the same towards guys. But he’s never been with a guy.

 _Maybe I should just mug him. No...The guilt will just drive me nuts and he didn’t do anything to deserve that...Just work your charm, Winchester. Do what you gotta do for Sammy._ When the guy turned his back to Dean, he looked around before walking around the back of his car to him.

Dean hesitated for a moment and looked around again before clearing his throat. The guy jumped and looked up at him, and Dean smiled. “Hi.” He was even more attractive up-close. Dark hair, the bluest eyes, and his lips. For a moment, Dean was in love.

The man asked “Excuse me?”

Blinking, the younger man asked “I’m sorry, what?”

The man turned to face him properly and said “I said “Uh, hi...Can I help you?””

Feeling his cheeks heat up, Dean chuckled and said “Oh yeah, sorry. And yeah, I was wondering if uh...If you wanted some company.”

His teeth caught his bottom lip and kept smiling even though the older man was clearly confused. “I’m sorry, I don’t know—”

“Oh, I think you do.”

“I’m sorry, I have a girlfriend.”

The younger man stepped closer and said “She doesn’t have to know. Hmm?”

The man studied him for a moment before looking around. “How much?”

Dean grinned at the victory and said “Two hundred sound okay, Baby?”

“For what?”

“Whatever you want.”

Nodding, the older man said “Okay. Get in, I’m almost done here.”

Dean nodded and got in the passengers seat and closed the door. He squirmed in his seat while he waited, trying his best to calm his nerves. _What the hell am I doing? No, no, don’t do that. Don’t wimp out, You can do this. You gotta do this. Do it for Sammy._

When the older man got in the driver’s seat, he put on a smile and said “Ready to go?”

“Yeah.”

“What’s your name, Handsome?”

“Jimmy.”

Dean nodded and said “Cool. I’m Dean.”

Even though Jimmy hasn’t looked at him since he got in, Dean understood. Wiping his sweating palms on his pants he asked “Soooo where do you wanna go?”

Jimmy paused for a moment and turned off the car before turning to the younger man. “Alright, I want to ask you something. And I want you to be honest with me here.”

Confused, Dean nodded and said “Sure, what?”

“How old are you?”

“Eighteen, why?”

“You’re eighteen? Honestly?”

The younger man nodded and said “Yeah, honestly. January 24th, 1979, I’m eighteen, what’s the problem?”

“The problem is you’re an eighteen-year-old kid who should be doing anything else but getting into strangers cars and trying to sell yourself.”

Dean frowned and said “You’re the one who wanted me in here!”

“Yeah, because I just wanted to talk to you. I told you, I have a girlfriend. Have you done this before?”

The younger man wanted to say yes, he wanted to lie and say he’s done this tons of times, but he could tell that this guy would see right through him. Dean sighed and said “No...But I need the money.”

“Where are your parents?”

The younger man crossed his arms over his chest and looked out the window. “Mom’s dead, dad’s busy.”

“Where do you live? I can take you home—”

“We’re not from here. We’re just in town for a couple weeks, staying’ at a motel here in town.”

Jimmy raised an eyebrow and asked “A motel? You’re not staying with relatives or something?”

“Nope. It’s me, my dad, and my little brother, that’s it.”

He instantly regretted saying that because Jimmy’s eyes went wide and Dean sighed. “ _Crap._ ”

“Little brother? Where is he, is he at the motel?”

“Yeah.”

“And how old is he?”

“Fourteen.”

“So your dad is _“busy”_ , and you left a fourteen-year-old boy alone in a note while you’re out here selling yourself?”

“Hey, he can take care of himself, he’s a tough kid!”

Jimmy rubbed his face and sighed. “Why do you need the money? Did your dad not leave you any money?”

Dean looked away again and said “He did, but...We had two hundred left and I thought I could win more for us by playing cards, and I lost it all...I told my brother that I was coming here to get snacks, and if my dad finds out, he’s gonna rip me a new one...Look, I’m sorry for bugging you, I just...I need help.”

He looked back at Jimmy and the older Roman said nothing while Dean continued. “And I don’t want you to call CPS, you look like you want to, but please, I’m begging you, do not do that. My dad’s been real busy with work and I promise you will never see me again after this. Please.”

Nothing happened for a while, they just studied each other. Then Jimmy reached into his pocket and pulled out his wallet. He pulled out three one hundred-dollar bills and held it out for him. Dean looked up and said “Wait, I just need—”

“Two hundred, I know. But here’s three, just in case. It’s alright, take it.”

The younger man slowly reached out and took the bills from his hand before stuffing it into his pocket. When he looked back up, the older man was now holding up a twenty. “You said you told your brother you were getting snacks, right? Well get some so he won’t ask questions.”

  
\\\\\\\\\\\\\\\\\\\•//////////

  
It didn’t take Dean long to pick out what he wanted, and he brought his armful of stuff to the counter. The clerk looked bored to death, and he barley paid any attention to Dean while ringing him up. When he came back out, he got back in the car and tried to give Jimmy back his change.

“Keep it. Where to?”

The younger man told him where to go and they said nothing for the next few minutes. He pulled into the parking lot and asked “You remember which room you’re in?”

“Yep. Just drop me off here, it’s fine.”

When the car stopped Dean unbuckled his seatbelt and said “Again, I’m really sorry I brought this crap on you. I don’t know how to thank you.”

The older man smiled and said “It’s no problem. Just don’t gamble your money next time, alright?”

“Yeah, definitely. Well uh, have a good night, I guess. Bye.”

“Bye, Dean.” Jimmy watched as the younger man got out and before he could walk away, he called out for him.

“Dean? Dean, hey.” Dean stopped and turned back around, bending down a little to look at the older man in the window.

“Yeah?”

Jimmy smiled and said “Take care of yourself.”

The younger man nodded and smiled. “You too. Bye Jimmy.”

“Bye Dean.”

He stood there a few minutes after he left before walking back to the room with a smile on his face. When he walked in, Sam said “ _Finally!_ What took you so long?”

“Sorry kiddo, the place was packed, and they only had one guy there.”

  
\\\\\\\\\\\\\\\\\\\•//////////

  
_**2008** _

  
Whoever pulled Dean out of Hell, whoever this _Castiel_ is, they’re here and they were ready. As soon as the barn doors burst open, they started shooting but the man wouldn’t go down. It took a minute for Dean to realize who he was shooting.

“Jimmy? Hey, stop. Bobby, stop!”

“What? Why?”

Jimmy stopped moving, his eyes never leaving Dean. Bobby came up beside him and asked “What is it? Why did you stop?”

“I know him.”

“Excuse me?”

The younger man nodded and said “Yeah. I met him a long time ago, I...I owe him three hundred bucks.”


End file.
